Allyl-formaldehyde-iso-sulfo-cyanate and process of making same.



Patented February '7, 1905.

iJNiTED STATES PATENT OEEIcE.

SIMON FABARON, OF PARIS, FRANCE, ASSIGNOR TO PIERRE LEON PIOT OF PARIS,FRANCE.

SPECIFICATION forming part of Letters Patent No. 782,016, dated February7, 1905.

Application filed June 15, 1903. Serial No. 161,487. (Specimens) To (0whom it may concern.-

1-1 N oset+N H :e

+2110]; 03H; S-O H; Carbonyl Allylamin. Iso-sulfo eya- Hydrochloricsnlfid. hate of allyl. acid.

(7)) sultid of carbon and allylamin we obtain H //NLI,C3I"I5 V csHs NH,CzsPIs Sulfid Allylamin. Allyl-snlfo-earbonate Sulfnreted of carbon. ofallyl.

hydrogen.

and by reduction Allyl-sulfo-carbon nate of allyl.

Allylamin. ate of allyl.

(c) bromid of allyl and iso-sulfo-cyanatc of potassium we obtain +KBr.SK SO3H Broniid of Iso-sulfo-eya- Iso-sulfo-cyanate Bromid of allyl.nate of penis of allyl. potassium.

Siurn.

If a mixture of hydrogen and carbonic acid is submitted to the action ofelectric sparks, a body is formed whlch plays the role or function ofaldehyde and Wl11Cl1 may be called it a l $3 I methanal, accordingtoHoimann,( iOlIIllC t 4 aldehyde or tormenol or tormol, ac-

' cording to Berthelot, or methylal, according to Gerhardt) and which iscommonly known as formaldehyde. The chemical formula of this aldehyde isaccording to the reaction Carbon ic acid.

H iH I H2O l CO Carbinol.

Oxygen. F0rmaldehydev OH \Vhen methylenic glycol, OH2 is pre 7 pared,this body does not remain in a free state, owing to the instability ofits molecule. It becomes dehydrated in forming formaldehyde, which isits anhydrid, but which trebles its molecule 3(OH2O) or 631160; the bodyname trioxymethylene.

Methylal in the form of trimethylal or of OH formaldehyde attacksglycerin, (13H; OH at OH, the temperature of about 200 centigrade,causes it to lose a molecule of water and, not being a saturated body,gives glycerie formaldehyde, which has not, as far as I am 5 aware, yetbeen mentioned by any writer.

This novel reaction is one of the bases of the improved process hcrelndescribed. Glyceric tormaldehyde may in presence of the elements ofwater regenerate by inverse reaction glycerin and formaldehyde ortriformaldehyde.

Aldehydes under special conditions give, with hydracids,ether-alchohols. Thus formaldehyde gives, with cyanhydric acid andsulfo-cyanhydric acid, the following cyanhydrins:

H N H ON ego 0% c H H H OH Formaldehyde. Oyanhydric Methylidenic mono- Hacid. cyanhydrin. 0:0 I t-on s-o3H. Glyceriozi n al- Iso-sulfo-cyanatedehyde. of allyl.

The process for the manufacture of formaldehyde-isosulfocyanate of allylis as follows: In a suitable vessel there is heated to about 190centigrade or more, if necessary, one kilogram of glycerin, to which isadded about five grams of iso-sulfo-cyanate of allyl, and the absorptionof a current of formaldehyde is caused up to the point where absorptionceases. The reactions take place in the manner indicated above, and theoperation is arrested when the weight of fourteen hundred grams isreached. Cooling is then allowed to take place and is followed byfiltering through paper. The product obtained may be employed eitherpure or diluted in all appropriate vehicles, such as glycerins,aldehydes, alcohols, acids, ammonias, ethers, water, and the like or anymixture of these vehicles.

Formaldehyde-iso-sulfo-cyanate of allyl is soluble in water, glycerin,aldehydes, alcohol, acids, ammonia, ether, or mixtures of thesevehicles. It boils at about 200 cent-igrade and has a clear yellowcolor, darkening in the light or when exposed to the air. It does not,so far as known, crystallize under any conditions.

Formaldehyde-iso-snlfo-cyanate of allyl is a sterilizer and anantiferinent. It may be employed for arresting all fermentation anddestroying all micro-organisms of ferments or soluble ferments Withoutexception, Whether they belong to the vegetable or animal kingdom,cellules or liquids, organic or inorganic, such as mushrooms,molds,yeasts, bacteria, neuro-epithelial cellules, vibrions, pepsins,

1:1 cN r1 soH Methylidenic monosulfo-cyanhydrin.

Formaldehyde. Sulfo-cyanhydric acid.

erating the glycerin, which recuperates the elements of water.

H s o-c.r1. on Water. Formaldehyde-iso-sulfo- Glycerin.

cyanatu of allyl.

pancreatins, maltins, virus serums, suppurations, and the like,(saccharomyces cerviside, penicillium glaucum. coccus pyogenes aureus,micrococcus, ureae, sarcin, and the like.)

I claim as my invention 1. The herein-described process of producingformaldehydeiso-sulfo-cyanate of allyl,- said process consisting incausing formaldehyde to react upon glycerin and iso-sulfo-cyanate ofallyl.

2. The herein-described process of producingformaldehyde-iso-sulfo-cyanate of allyl, said process consisting incausing formaldehyde to react upon glycerin and iso-sulfocyanate ofallyl under heat.

3. As a new product, the herein-described sterilizer and antiferment,consisting of formaldehyde-iso-sulfo-cyanate of allyl'and having theformula:

and soluble in water, glycerin, aldehydes, acids, ammonia, ether, ortheir mixtures, boiling at about 200 centigrade, and of a light yellowcolor, darkening on exposure to light or air.

- In testimony whereof I have signed my name to this specification inthe presence of two subscribing witnesses.

SIMON FABARON. [L. s.]

l/Vitnesses:

LEON FRANOKEN, J. ALLISON BOWEN.

